Sodium Carbonate → HCID 24966725, compound

HRID 545634Notes

Reaction equation

HRID 545634 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:7](=[O:19])[NH:6][CH2:5]2.[CH:20]1([NH:23][C:24](=[O:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:26]=2)[CH2:22][CH2:21]1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:27]3[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=3[CH3:31])[C:24]([NH:23][CH:20]3[CH2:21][CH2:22]3)=[O:41])=[CH:11][CH:10]=2)[CH2:5][NH:6][C:7]1=[O:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 67189327HCID 67189327, compound

Product 1

HCID 24966725HCID 24966725, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred mixture of 6-bromo-1-(2-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one (0.1993 g, 0.5903 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.2134 g, 0.7084 mmol) and Pd(PPh3)4 (0.03411 g, 0.02952 mmol) was added 1,2-dimethoxyethane (5.000 ml) followed by 2N Na2CO3(aq) (0.7379 ml, 1.476 mmol) under nitrogen. The mixture was heated to reflux for 24. After cooling, the mixture was filtered through a short path of Celite and the filter cake was washed with EtOAc (3×10 mL). The combined organic layers were concentrated to give a crude product, which was purified using flash column chromatography (50% EtOAc in hexanes to 100% EtOAc) to afford 3-(1-(2-chlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-6-yl)-N-cyclopropyl-4-methylbenzamide as a white solid. MS m/e 432 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through a short path of Celite
  5. washthe filter cake was washed with EtOAc (3×10 mL)
  6. concentrationThe combined organic layers were concentrated
  7. customto give a crude product, which
  8. customwas purified

Sources & evidence

ORD record
ord-ef70ba7625f743e39a4db09204e3ec8d
Source dataset
uspto-grants-2011_05
Patent number
US07935709B2

Reaction notes

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